


The Angel of Thursday and The Righteous Man of Chicago

by Insanefangirl



Category: Supernatural
Genre: Castiel Acts Like Endverse Castiel (Supernatural), Criminal Castiel, Detective Dean Winchester, Drug Use, F/M, Hurt/Comfort, Lawyer Sam Winchester, M/M, Protective Castiel, Protective Dean Winchester, Protective Sam Winchester, Tattooed Castiel, Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-06-22
Updated: 2020-06-22
Packaged: 2021-03-04 03:47:40
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 16,634
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24867070
Author URL: https://archiveofourown.org/users/Insanefangirl/pseuds/Insanefangirl
Summary: Cas Novak has been apart of his sibling’s gang since his father left the picture years ago. When he saves Detective Dean Winchester, The Righteous Man of Chicago, he thinks maybe this drugs and crime under his siblings isn’t how he wants to live his life.
Relationships: Castiel/Dean Winchester, Sam Winchester/Jessica Moore
Comments: 1
Kudos: 37





	1. Prologue: The Middle Finger is My Favorite way to say Hello

**Author's Note:**

> I own nothing, obviously

Electric blue streaked it’s way across the old brick, completing the mural. It was a beautiful city scape behind aggressive, straight, gray jail-bars. A city in prisoned. The blue streak over wings was his signature touch. The Angel of Thursday. Graffiti artist of the streets of Chicago. 

He stood back from his work to admire it. It was beautiful, with the city scape against deep reds and oranges and yellows. Like a sunset. Or like a fire. 

Castiel Novak was lost as he scrutinized his work. A crackle of the walkie-talkie in his bag woke him from his trance. 

“Castiel, would you focus?” Michael’s voice came through the device. “I’ve asked if it was clear twice now.” 

“Yes, it’s clear, Michael.” Cas sighed and his oldest brother didn’t respond. 

He went to sit in the driver’s seat of the car. As the youngest of the Novak family gang he played lookout and that was fine by him. The family business sucked ass and so did his siblings. 

The Novaks had been terrorizing the city since their father left fifteen years ago on a bender when Cas was thirteen . His mother had never been in the picture so twenty-six year old Michael took over and they turned to crime. 

Doors open and Cas’ seven siblings all piled into the car and Cas pulled away from the fancy office building. Few details were shared with Cas, but from what he knew they were in business with one of the higher ups of the company. For either money, drugs, or resources he didn’t know. 

He meandered his way to the apartment building they owned in order to avoid the main traffic. His siblings were silent, they weren’t the fucking Brady Bunch and no one was pretending they were. 

Parking the car, Cas slammed the door behind him and made his way into the building. His siblings took the elevator while he continued his stomping up the stairs to their penthouse at the top.

The building had been bought while empty and falling apart. With the money stolen/gotten from drugs and what-not had been put into updating it into a luxury apartment building for the rich and powerful to live under Michael’s thumb. 

By the time he got to the top floor his siblings had all retreated to their respected rooms. Cas did the same and let out a breath as he leaned against the now locked door. 

“I need pot.” Cas mumbled as he lifted his black hoody over his head. He began to rummage the dirty room for his stash. As long as he promised to be sober while working, Gadreel, in charge of the drugs, didn’t care if he took some for himself. 

Cas enjoyed playing the rebellious little brother at home and the too-cool-for-you-to-even-look-at-me sketchy guy on the streets. It gave him satisfaction and he looked the part. 

Joint in one corner of his mouth he took count of his tattoos in the mirror. 

Enochian scrawled on his ribs so angles couldn’t find him. Considering his siblings were all named after angels he found it fitting. 

A garden grew its way from his hip to his neck in a multitude of different colors and types of flowers. A blue rose exposed above his shirt collars. 

Open gates in grey scale on his other side. Surrounding it was the galaxy with all the planets in rich colors covering the rest of the exposed skin of his torso. 

His hands had the bones underneath skeptched onto the top skin to provide x-ray to underneath. Some were drawn as shattered or chipped.

Each and everyone of his tattoos was meaningful and special, but his wings were his favorite. They took up his entire back and ran down his arms to his wrists to give way to bone. They were in deep blue ink. Looking at them made him feel like he could fly. 

The piercings encasing his ears, one on his lip and three in his eyebrow, had been more to piss his siblings off. Michael, Raphael, Anna, and Hannah always looked at them with dismay that made him smirk. The others didn’t care. As long as his siblings were busy, they didn’t care about Cas either.

Regardless his additions still felt like apart of him. Making his body his. Forging it to be armor to protect his heart.


	2. Welp This is All a Mistake

**Summary for the Chapter:**

> Angel of Thursday meets the Righteous Man of Chicago, not that he knows that yet.

**Notes for the Chapter:**

> My first attempt at writing smut, not my first time reading it for sure.

Cas was not having a good day. He had been called up to Michael’s office, before noon, to once again have the ‘You’re Distracted’ Castiel’ talk. This one included the overplayed hits, such as ‘You need to focus, Castiel’, ‘You should be more invested in the family business,’ and his favorite ‘And while you’re at it, please take out those stupid piercings, they are an absolute eyesore.’ Cas just stood there, staring at his favorite part of the floor, with a cigarette between his lips, until Michael gave up.

Then he went outside to escape it all, find a nice blank wall, but it was hot. Like steamy eighty degrees hot. In his black shirt and black skinny jeans it wasn’t comfortable.  
On top of it all he had left his wallet back at the apartments in his rush to escape and he was out of cigarettes.

So now he was moping his way into downtown Chicago on his way to his back alleys to let off a little steam. 

He ran his fingers through the blue tips of his sweaty black hair with a huff. What he really needed was a smoke of something maybe a little stronger.

A squeal of tires broke him from his thoughts. He looked up to see a car blazing down the street and a man in the crosswalk. 

Cas wasn’t the saving type. He wasn’t supposed to draw attention to himself and he normally didn’t. If anything a man getting hit by a car could prove to be entertaining. 

So why Cas threw himself at the stranger, pushing them both out of the way of the speeding car was beyond him. He must have been possessed by the devil or some other demonic being. 

Whatever the reason, he found himself laying on top of an utterly gorgeous man. Green eyes, tan, freckled skin, buzzed dark blond hair. Dressed in jeans and flannel this man looked like the poster all-American boy. 

“You my guardian angel?” The man said with a teasing smirk. That voice. Cas wanted to paint it. It was deep and just this side of southern that turned Cas’ insides to liquid. 

Realizing he was still lying on top of this handsome man in the middle of the sidewalk, Cas quickly scrambled off. The man got to his feet and smiled at him. 

“So,” he began in that voice, and oh Chuck, his legs are bowed. “When someone saves my life I normally owe them a drink. I’ll do you one better with dinner.” 

Cas was sure is brain was ran over by the car because words aren’t leaving his mouth. 

“I mean don’t feel like you have to or whatever, but-“ the man scratched the back of his flushed neck. 

“Cas.” Finally escaped his mouth. 

“Sorry?” Confusion was written on his face, beautiful face. 

“My name is Cas.” 

“Cas? What’s that short for?” Dean was grabbing his hand and writing on it. “How about you tell me over dinner? Roadhouse? 8 o’clock? My treat.” There was that smile again that made his boxers want to drop on their own. 

“I’d like that.” Cas offered his own smile. 

“See you then, Guardian Angel.” And with that he was gone, walking down the street. 

When the spell was broken Cas looked at his hand and saw a phone number and a name. 

“Dean.” Very fitting. 

Cas hiked his paint bag over his shoulder more and walked, lost in thought, to a wall deep within the maze of alleys.

He had been going to paint his anger away. Maybe more steel bars. Now he found himself reaching for the green and spraying a large oval. 

——————

8 o’clock rolled around and a freshly showered and dressed Cas walked into the Roadhouse. 

It was a bar, not normally his type of place, if he wanted a drink he went to a club. Seeing Dean in a booth in the back made him feel like there wasn’t any other place he would rather be. 

Green eyes locked on to his and Cas made his way over. He was dressed in jeans and a grey Henley that made Cas glade he hadn’t bothered to get too dressed up. A dark blue button up with a clean pair of skinny jeans without paint and only one hole.

“Hello, Dean.” Cas took a seat across from him. 

“Hey, glade you showed up.” 

“Wouldn’t have said I was going if I wasn’t.” Cas had his head reattached to his body finally. A smoke outside helped his nerves tremendously. 

“Wouldn’t be the first time I was stood up.” 

“With a body like that?” Cas leaned forward slightly, “ impossible.” 

Dean gulped and waved down the waitress. 

“Ah, Dean, your date lives after all.” The blond waitress welcomed as she approaches them. 

“Come on, Jo, you really have no faith in me?” Cas watched their interaction, she’s clearly a close friend to Dean. 

“Well, me and Ash were getting a betting pool going.” Jo joked. 

“I get to see any of the money?” Dean shot Cas an amused look. 

“Not a chance, Dean-o.” A man with a mullet called from behind the bar. 

“So what’ll you boys be having?” Jo took out her pad and gets to business. 

“Usual for me,” Dean handed her back the menu. “Cas?” 

“Just a cheeseburger and a whatever you’ve got on tap, please.” Cas also handed the menu back. 

“Oh good,” Dean sighs in relief once Jo walked away. “I was half expecting you to be a vegan or something.” 

At Cas’ raised eyebrow he fumbles. “I mean not that there is anything wrong with that or anything. But.” He scratched the back of his neck. “Burgers.” 

“Yes, burgers.” Cas replied gravely with an amused smirk. “You must come here often.” 

“Yeah, the owner, Ellen, is a close family friend. Jo is like a sister to me.” Cas was unsure what to say so he just hummed in acknowledgement. 

Jo set their beers down silently before leaving again. 

“So, Cas.” he took a sip. “What do you do for work?” 

“Family business.” Cas replied shortly. He may have never been on an actual date, but he was sure ‘I work for my family’s business that practically owns this town through money, drugs, and violence’ wasn’t first date material. “I work in logistics and it’s all very boring.” Well, it was not a complete lie. “You?” 

“Detective.” Of fucking course he was. “It’s not very boring at all.”

“I imagine not.” Cas should leave. Though a relationship outside of a equally powerful person that Michael approves of would be a great act of rebellion, a cop was just plain stupid. 

Their food comes, the smell alone made Cas consider staying for the meal. Dean’s sibling like banter with Jo decides for him. 

They both bite into their food and Dean let out a border line pornagraphic groan that made Cas’ dick twitch slightly. 

“Do I get to hear what Cas is short for now?” Dean asked between bites. 

Cas contemplated that thought on the burger. “I suppose.” He drawled after a bit but continuing to eat. Dean had set down his burger and was looking at him intently. Cas dragged out his chewing just to tease him. 

Finally he swallowed and continued “Castiel.” 

“Like the angel?” 

“How’d you know he was an angel?” Cas was impressed. He was smart, funny, fucking hot, adorable, and a damn cop. Cas was screwed, but he was having so much fun. 

“Family friend had a lot of biblical books so that’s what I read to my brother growing up.” Dean seemed to have a lot of family friends. Cas wondered the nature of these ‘friends’. 

“Interesting.” Cas took another bite of burger. “I’ve got to say, you’re the first to catch on.” Hope he doesn’t catch on to anything else. 

“What can I say? I’m full of surprises.” There’s that lop sided smile that Cas could bathe in. 

“I’m sure.” Noticing they were both done with their burgers Cas added. “Want to show me?” Wicked grin on his face. 

“Hell, yeah.” Dean slapped down some bills on to the table. “My place?”

“Yeah, my roommates a bitch.” Understatement. 

“We can take Baby. You walk here?” 

“Yeah I walked.” Cas followed Dean out the door. “Baby? Am I walking into a threesome?” 

“No,” Dean blushed. “She’s my car. Pride and joy.” They walk up to a sleek black Chevy. 

Dean unlocked the passenger door and opened it for Cas like a gentleman. Once he gets in the car he leaned over to kiss Cas. Softly, like he’s testing the waters. Cas is more then happy to respond. 

Next thing he knew he was laying on top of Dean on the bench seat. Dean’s hands are firmly on Cas’ ass. Tattooed arms braced on either side of Dean. Lips wherever they can reach. 

“We didn’t get very far.” Dean chuckled breathlessly. “As much as I love making out in Baby, my bed is memory foam.” 

Cas chuckled and stole one more kiss before he got off Dean for the second time that day, and hopefully not the last. 

The ride to Dean’s apartment was short but too long all the same. They continue their kissing in the elevator to his floor and have to stop multiple times in the hallway. 

Dean unlocked the door and led Cas into the apartment. It was dark but Cas can see it was a decent size. He doesn’t get to investigate though because he had more important things to do. 

Such as pressing this sex on legs of a man against his own bedroom door. He ate Dean’s moan right out of his mouth. 

He spun them and walked Dean to the bed. For the third amazing time that day Cas was on top of him and he’s grinding his hips down as Dean does the same. 

“Cas.” Dean groaned. He unbuttoned Cas’ shirt and pushed it off his shoulders. Cas returns the favor. Making note of a horned brass amulet that had been under his shirt. 

“Wow,” Dean breathed out, eyeing Cas’ ink. He trailed his fingers over the enochian script, his fingers left a trail of goose flesh.

“You’ve got lube, sweetheart?” Cas slowly undoes Dean’s pants. 

“Top drawer of the nightstand. Condoms too.” Dean’s hands are on the waistband of his jeans.

“Jesus, how do you get into these things?” Dean muttered, staring at Cas’ thighs. He knew he had a runner’s body, it was another way for him to burn off steam. 

“Aren’t you more interested how I get out of them?” Cas nipped at Dean’s ear and was rewarded with a sharp gasp. 

Cas walked over to the nightstand, loosing his pants as he went. He grabbed the lube and a condom. Turning back to Dean he almost wants to drop everything and just paint him on a wall all for himself. 

Dean was spread out on the bed, naked, out of breath, and staring at him. Green eyes baring into his own. Finally blinking Cas dropped his boxers and crawls back on top of the gorgeous man. 

Kissing a trail down his chest to his inner thighs, Cas thumbed the other man’s nipples on the way. He was pleased to see how sensitive Dean was. 

“Someone’s responsive.” Cas teased as he sucked bruises into Dean’s inner thighs. 

“Someone’s a fucking tease.” The man under him gasped. 

“Patience.” Cas felt a smirk break his face and he licked a long stripe up Dean’s cock. Successfully shutting him up. 

Sitting up and ignoring Dean’s honest to God whine, Cas drenched a finger in lube. He began teasing Dean’s hole before slowly slipping a finger in. 

He worked him open slowly until Cas had three fingers inside and Dean was a squirming mess before him. 

“Cas, Please! I’m ready! Please, please.” Cas swallowed Dean’s pleads, finding them just as delicious as they sounded.

He backed up again and rolled a condom on his raging hard on. Then he slowly pushed in, pausing occasionally to allow Dean to adjust. 

Once he was balls deep and Dean was withering underneath him Cas began moving again. Deep and quick thrusts, searching for that sweet spot that’ll make those pretty green eyes see stars. 

“Cas, Cas, Cas. Fuck.” Below him, Dean was babbling and Cas had never heard something so beautiful. If he was in his right mind, not balls deep in a gorgeous man, he would probably be more concerned about that train of thought. 

He felt heat curling in his gut and he could see Dean was close too. He grabbed Dean’s neglected cock and stroked it feverishly. Three more deep thrusts and strokes and they’re both coming. 

Cas collapsed onto Dean, both of them catching their breaths for a few minutes. He then slowly pulled out and removed the used condom. Grabbing a tissue from the nightstand he began moping up the jizz from Dean’s stomach. 

Exhausted, Cas collapses once again next to the green eyed man. 

“I should go.” He confessed, begrudgingly moving to get up. 

A hand on his wrist stopper him. 

“Just stay the night, please.” Well, Cas couldn’t argue with that logic. He dropped back into bed and slung an arm over Dean’s torso and snuggled closer. Before he knew it, he was asleep.


	3. What Is and What Should Never Be are the Same Fucking Thing

**Summary for the Chapter:**

> Cas is screwed and not in a good way. He even attempts to distance himself from the Righteous Man but the universe has other plans.

Cas woke up mildly confused. For one, he was naked. Now it wouldn’t be the first time but he definitely never fell asleep with a living furnace next to him. That was the only way to describe it too, he was under a living, breathing heater. 

He dragged his eye lids up and saw Dean. He was still asleep, snoring softly on Cas’ shoulder. Last night came back to him and he couldn’t help the smile on his face. 

He could stay in bed forever but his bladder had other ideas. Reluctantly, he untangled himself from the other man and sheets alike. He left the bedroom in search of the bathroom. 

He found it across the hall and gladly took care of business. 

Afterwards he saw it was eight and a weekday so he figured there wasn’t time to crawl back to bed. Instead he located the kitchen and started the coffee maker. 

Looking around he noticed lots of photos. Pictures of smiling people both with and without Dean in them. A tall man with long brown hair is frequent in them. 

What caught Cas’ attention was a badge in bowl with a pair of keys. He knew he probably shouldn’t touch an officer’s badge, by some unwritten code or whatever. However he couldn’t help himself, curiosity kills the cat and all that shit, so he reached for it.

Quickly, he dropped the badge as if it burned him. Oh shit. Oh fucking shit. He took another look just to be sure. 

Of all the guys and all the streets. Castiel had to sleep with Dean fucking Winchester. Chicago’s fucking Righteous Man.

Cas was going to bet his entire drug stash that the tall man in the pictures was Sam Winchester, Dean’s partner in crime. 

He needed to leave yesterday. As silently as he possibly can, he returned to the bedroom to grab his cloths. Changing in the living room he’s out the door and sprinting out of the building. 

“It’s the walk of shame not the run of shame, buddy!” A man in the lobby shouted and Cas doesn’t stop to pick a fight. 

He ran and ran until he ran into Hannah. 

“Castiel, where have you been?” Disappointment was traced into her features, but Cas was too busy trying to catch his breath. 

“Good to know my absence was noted.” Cas walked past her to his room. 

“It’s noticed Castiel,” Hannah called from behind him. “But it won’t be tolerated much longer.” 

“Whatever the hell that means.” Cas grumbled before slamming his door shut. 

God he needed a smoke. Rifling for his stash he lit a joint and collapsed into the bed. He held the smoke in before letting it out his nose. 

Dragging his earbuds from under a pile of cloths, he plugged himself into music to think. 

He knew a lot about Dean Winchester, the whole city did. His siblings were especially interested in the detective. 

He was born in nowhere’svill Kansas. Records show he and his little brother were dragged across the country by their father until Sam graduated high school and left for Stanford, Dean followed. 

As Sam worked for a law degree, Dean got his GED and graduated from Palo Alto’s police academy. He was promoted to detective and was transferred to Chicago, his brother followed a year later with a law degree under his belt. 

He took another drag, allowing the chemicals to mess with his brain. 

The brothers didn’t hit the news until three years later. Dean got Azazel Yellow, a powerful weapons distributer, in a cell on the grounds of too many parking tickets. His brother then blew the entire operation wide open and wiped it out. 

A year later the elder Winchester was known as the Righteous Man of Chicago after he was captured, escaped, and arrested the notorious serial killer Alastair De’mon. 

Since then the brothers had been burning each crime operation in the city down to the ground one by one. The Novaks had been lucky, kept everything squeaky clean on the surface, but Cas knew his siblings were worried. 

And Cas just had dinner and mind-blowing sex with him not 24 hours ago. Another drag. 

Switching gears Cas began to look at the facts. What was the probability that he saw Dean Winchester ever again? It was a big city and he didn’t think they had ever crossed paths before. 

Second, even if they did cross paths it was one date, plenty of people left after the first date and were never heard from again. 

Thirdly, Dean didn’t even have his phone number so he had no way of contacting Cas himself.

One more drag before flicking the bud to the other side of the room. So Cas was off the hook. He had a good one night stand and that was the end of it. 

Peace of mind in tact, Cas took a shower and went to get breakfast. 

“Castiel,” Lucifer was sitting in the kitchen. “Mike wants you to pick up some files from the library today at noon.” 

Ah yes, in addition to get away driver, Cas was also a glorified errand boy. A glance at the clock said that it was only eleven. He had time to eat breakfast before he had to get to the library. 

“Fine.” He replied as he grabbed from his stash of pop tarts, his siblings only eat omelettes, grapefruit, or eye of newt for breakfast. 

“Fun night?” Lucifer asked with a smirk. 

“What?” How could he possibly know? About Dean? About-

“Hannah said you didn’t come home last night.” 

“It may have escaped you,” Cas huffed. “But I am a legal adult. Can vote and everything.” 

“Yes, between the bad-ass emo look you’ve got going on and the bitchy attitude, must have escaped me.” 

Cas just walked away. He had neither the time nor the patience for this.  
——————

The air conditioning as Cas entered the library was greatly appreciated, though it was much cooler then yesterday, the blast of the overrun AC in the early fall weather was refreshing. Even more so when one considered the suit he had to wear for appearances on these little errands. 

Cas walked directly to the back of the building to the offices. Making sure to pull his shoulders back in order in order to look confident, or like a pompous ass, which ever you prefer. 

Crowley was in the last room on the left. He was a short, rodent like man with a well known reputation to give any information away to anyone for a price. The man had no loyalties to anyone but himself, hence his siblings mistrust for him. 

They always met in a mutual, public location and there was never any small talk. Strictly business. That’s what Cas liked about meeting with Crowley, no politics or sentences you had to dissect in order to find their hidden meaning. Get the files and get out. 

“Mr. Novak.” Crowley greeted. “You’re looking especially prickly today.” 

“Crowley.” Cas set the brief case, yes a classic brief case, on the table. 

Crowley’s two goons open it and thumb through the money. The Novaks weren’t known for skimping, but one could never be too careful in this line of business. 

One of the goons nodded once the money was counted and another brief case was set on the table. Cas idly wondered if people in this business just let the brief cases circle through. They all looked the same anyway. 

Cas opened it, scanning the files inside to make sure they are correct, before snapping it closed again. 

“Pleasure doing business with you, darling, as always.” Crowley said and left the room, flanked by his goons. 

Cas waited the appropriate time before leaving himself. Brief case in hand he loosened is already loose tie as business is completed. 

“Hey, Cas.” Oh shit. 

There he was, Dean fucking Winchester, in the library. This library that Cas just did an illegal transaction and was now holding a case full of stolen files about people and things that wouldn’t live to see the near future. 

“Hello, Dean.” Thankfully his voice doesn’t shake like he was on the inside. 

“Grabbing something for work?” He eyed the case and Cas resisted the urge to hide it behind his back. 

“Yeah, just some papers.” Looking him up and down. “I suspect you aren’t here for work.” Dean was wearing well worn jeans, t-shirt, and flannel with a pair of equally well worn boots. Which he is thankful for as he doubts he could handle Dean in a suit anymore then he could his birthday suit.

“More off-duty stuff.” He shrugged “Helping Sammy with a little research.” 

Great Sam was here, let’s just get a big party going of all the people Cas Novak should not be in the same room with. 

“I’m sorry if I’m bothering you. I honestly didn’t think I was going to see you again after you left this morning.” That was the plan. Dean continues, “thanks for the coffee by the way.” 

“You have horrible taste in coffee.” Why was Cas responding? Why was he even still here?

Dean’s laugh answered him. “Hey, you like that shitty, sugary, girly stuff you’re going to have to talk to my brother.” 

“It’s tar, Dean.” Leave you idiot! 

“It’s fuel, Cas.” Dean’s got a smile that reached his green AF eyes. “And with how much I drink it I don’t think I can afford the extra calories.” 

“None sense. I’m sure you’d look just as fuckable no matter what.” 

They lull into silence and there is still no reason for him to be here, flirting with the guy he had previously decided to never see again. Heaven hated him is the obvious answer. 

“Look,” Dean started. “I’ll respect if you just want to be friends or nothing at all, but I had a good time last night and you did too...” 

“D-“ It’s a good thing Dean cut him off because he didn’t know what he was even going to say anyway. 

“Not that I know you really well or whatever, but reading people is kind of in the job description and you weren’t hiding it or anything. And-“

“Dean!” He got those green orbs to snap to his. “I did have a good time last night. Not even just the fucking, even though that was equally amazing,” Dean smirked, “I left unexpectedly. I planned on staying until you got up,” truth, “but then a work thing came up and I rushed out without thinking of leaving a note,” lie -mostly. 

Dean visibly relaxed and Cas felt a little bad for lying. Even almost lying. 

“Good. Yeah that’s good. So...” 

“Here.” Cas grabbed a paper and pen from a near by desk and wrote his number on it. He handed it to Dean with a smile. 

Dean is about to say something when a tall man -taller then Dean, who already had about an inch on him- bonded up to them like an over grown puppy. 

“Hey, Dean.” And It’s none other then Sam fucking Winchester. “I think we can call it a day for now.” 

Sam was looking at Cas. From his polished, barley worn, dress shoes, to his messy blue tipped hair. 

“Who’s this?” Sam asked innocently. Shooting his brother a look Cas can’t read, but Dean apparently can because he sent Sam a death glare that definitely does not turn Cas on a little. The brothers really are psychologically connected. 

“This is Cas.” Dean explained shortly, clearly annoyed with his brother. 

“Sam Winchester, nice to meet you.” Sam stuck out his oversized hand to shake and Cas stared at it for three good seconds before shaking it. Dean looked ready to hit his brother who looked like he’s enjoying himself too much. It was very entertaining watching the two interact. 

“So, Cas, Dean tells me you saved his life.” A glance at Dean shower him red tipped ears. 

“Yes, well, right place, right time and all that.” Cas stifled the urge to pull his lip stud into his mouth to suck on in a nervous tick. 

“Mm.” Was all Sam says. 

“Well.” Dean saw his opportunity to interject. “Sammy has to get back to the office. It was good seeing you again Cas. I’ll call you later.” He took his brother’s arm and begins to practically drag the giant of a man out of the library.

“Wait!” Sam called, digging his heels into the cheap library carpet. “Dean was going to get lunch. Cas, Dean tells me you eat. Why don’t you join him?” 

Before Dean can strike him dead, Sam was gone, leaving Cas and Dean with an awkward tension. 

“Did your brother just ask me out on a second date for you?” Cas needed clarity. 

“Yeah, he’s a bit of a bitch.” Dean rubbed the back of his neck. “But I mean if you want to I was planning on getting lunch, you do eat after all.” 

“Yes well, my robotic programming does now include all the human body functions.” Dean snorted at him. 

“Okay, C3PO.” 

“Who?” Cas is rewarded by Dean’s appalled face. He had decided all of Dean’s faces were equally gorgeous. 

“Star Wars, dude!” Cas gave him a blank look in return. “Are you doing anything right now?” 

Cas eyed the brief case. “Yes, but I have time for lunch. And I’m free tonight.” What the hell was wrong with him. Apparently his new programming failed to include common sense. 

“Great!” Dean took his hand. “Come on, I know a great cafe.”


	4. Cas is Cool as a Cucumber

**Summary for the Chapter:**

> Cas is getting in too deep with Dean and his family, he should be scared but he can’t bring himself to be.

Cas hadn’t tried to get so close with the Winchesters, he really hadn’t, but it was as if some cosmic entity was having a grand old time fucking with him. 

After the movie marathon date with Dean, Cas found himself purposely in his company at least three times a week. They had dinner, watched movies, sometimes just take drives in the impala and talk or just sit in comfortable silence.

So Cas told himself it’s just about the sex. That’s all this relationship was to him. A long -really long- strung out one night stand. It wasn’t that hard of an argument to make, the sex was amazing and frequent. 

Then two months later Dean was telling Cas about his childhood, going days without food so his brother could eat. How Bobby, the police chief, Ellen, who ran the Roadhouse, and her daughter, Joe, were like family to him and Sam. 

So Cas told himself he has no control what Dean wanted to spill on him. He’ll simply enjoy the sex and keep to himself. 

Then he was explaining to Dean in detail the personal meaning behind each tattoo. How the flowers on his torso and neck reminded him of brilliant life outside the concrete city. The Enochian protecting him from angels, his siblings. Open gates with the galaxy representing freedom and reminding him of a vast universe. His hand bones a badge of his violent childhood, the fights, both provoked and not. Finally his wings, an angels like his namesake, how they would carry him away one day. 

After that night he even tried to feigned sickness for a week to avoid Dean. It doesn’t work, he made it through one day of no contact before he broke. He even asked his siblings for more responsibility in the company to keep him occupied while Dean was at work. His siblings were fucking thrilled. 

So he pacified himself by saying he’ll keep it just between the two of them. Next thing he knew he was taking weekend jogs with Sam Winchester. They’re signed up for a marathon in the fall. Dean teased him everytime about only running if being chased, but he gave him a kiss even when Cas was all sweaty. 

His next weak attempt of an excuse was that he reasoned he can’t be in a relationship (a strictly sexual relationship) with Dean Winchester without being in his brother’s company at times as well.

Then he was invited for Thanksgiving and Jess, Sam’ wife, announces she’s pregnant. Next thing Cas knew they’re in bed and Dean mentioned (totally without any pressure) that he would like kids in the future day. Cas couldn’t stop himself from think what an amazing dad Dean would be.

It’s been eight months and Cas has stopped attempting to argue with himself that he had a reason to stay with Dean. He was sleeping there at least four times a week and spending most days seeing him at least once. His siblings have stopped asking where he goes as long as he gets his work done. 

Dean even asked him to move in at month six, but Cas said he had to wait for his lease to be up. It wasn’t brought up again. 

Month nine is wrapping up and Dean found out about his grafiti. How he didn’t before Cas had no idea, he was a detective. Cas is sure it’s over. Graffiti was illegal. Dean was a cop. Case closed. 

Heaven hated him. Dean was all fucking understanding and supportive, saying it’s art and it makes the boring cement walls look so much better. He said as long as it’s not hate or anything, there’s really no problem. The Righteous Man even went a step further, gave Cas that teasing smirk were he can see Dean’s tongue between his teeth, and told him it’s below his pay grade anyway. Cas kissed the smirk off him and Dean used his tongue to tease Cas’ lip stud instead. 

So this was how Castiel Novak found himself showing his illegal art to Dean fucking Winchester in the alleys of Chicago. 

“Wow.” Dean gasped as they approach one of his older pieces. It was a gray scale skyscraper with a winged man stepping off. Cas’ signature blue streak slashed through it. “This is your mark?” Dean placed a hand on the streak. 

“Yeah.” Cas felt a little embarrassed. He knew it’s a good piece, but seeing Dean stare at it left him feeling bare. Like his final wall was being breached. 

“The guys at the station call you the Angel of Thursday.” Dean said as he traced the winged man. 

“Why?” Cas hadn’t known his art had caught any attention. 

“There was a pursuit one night.” Dean didn’t look away from the wall. “It was storming and we were chasing Alastair. He had goons everywhere. We lost a lot of good men. I shouldn’t have been working that night, I was barely cleared from the hospital after it all.” Dean hadn’t talked about his time with Alastair, but Cas had seen the scars, had traced them softly with his lips. 

“But I needed to do it myself. Want something done right you have to do it yourself and all that. We chased him and his goons through the alleys all night. Finally, I had him cornered. I wanted to kill him. He had tortured me for four months. I wanted to so bad. But I tased him instead. And kicked him around a bit.” 

Dean paused and Cas felt anger rise up in him for what was done to his Dean. 

“When I looked up. The sun was just rising and this was the first thing I saw.” Dean rubber a thumb over a dark stain at the bottom of the mural Cas didn’t paint and he choose to believe it wasn’t Dean’s. 

“We didn’t think we’d make it through the night, but us lucky ones made it to Thursday morning. I wasn’t the only one who had their first moments that morning against your work. Like five other officers said they saw the most amazing art with a blue streak across it. Made them feel like the world wasn’t as ugly as that night had been.” 

Cas had tears in his eyes when Dean finally looked at him. 

“Oh, sweetheart.” Dean pullEd him into a hug and kissed his temple. 

Cas felt guilt from the lying crawling up his throat in the form of vomit. Dean was baring his soul and Cas hadn’t even told him his last name. 

Dean held him there in the alley, were he chose to spare his torturer. The torturer who Cas’ family had hired to rid them of Dean’s meddling in their operation. 

He didn’t know all the details, but he knew his siblings were not happy when Dean lived and continued with his brother to take fight evil in the city. 

They stood there for awhile before Dean suggested they go home. Not to Dean’s place. Home. Cas just nodded mutely and followed. 

They curled into bed and Cas fell asleep by trading lazy kisses with Dean. 

When he woke up, Dean was in the kitchen wearing Cas’ paint splattered shirt with a fresh plate of chocolate chip pancakes for him. Cas felt like crying again. He didn’t. 

He ignores the plate, backed Dean into the counter and kissed him. 

“I love you.” Escaped his lips before his brain had the opportunity to butt in. 

“I love you too.” Dean gave him that lopsided smile and Cas couldn’t stop himself from kissing it off him. 

Cas was officially in over his head.


	5. Flaming Shit Has Hit the Fan

**Summary for the Chapter:**

> Things are good. Until they aren’t, naturally.

**Notes for the Chapter:**

> More smut to be warned

“We’ve got a big lead tonight.” Dean said from Cas’ lap. Cas was running his fingers through the other man’s hair while not really listening. 

He probably should be, as it was work related, but he had long ago given up on pretending he was doing this for any other reason then that he loved Dean Winchester. Yes love, they say that now. 

So he allowef himself to drift. Lost in the thrum of Dean’s slight southern drawl and the rhythm of his hands moving in Dean’s spiked hair. 

It had been ten months since they had started dating. Everything was good. He had been clean for the last three months now, Dean didn’t know of course. He was the reason Cas had quit. There had been times it sucked out loud, but Dean had managed to distract him without even trying. 

He felt good. Dean made him feel good. His family had noticed his mood shift and his absence. They had only mentioned it a few times, Cas had answered sharply about being a grown ass adult and it was now left alone. They were very pleased about his larger roll in the company after all. Cas didn’t care, as long as it kept him busy, Dean unaware, and his family content. 

He was in love. He was loved. Dean fucking Winchester loved him. That thought still had butterflies fluttering in his stomach. Dean’s family loved him. They had taken him in and added him to their rag-tag family. Sam and him had gone out for drinks when Dean and Jess worked late one night. He and Dean had joined Jess and Sam on double dates once a month. 

That part of him that was worried about justifying his actions and his feelings had long shut up and gone with the flow. 

A pressure on his groin snapped his head away from his thoughts. 

“What?” 

“Pay attention to me!” A grown man whining should not be as adorable as it was. It probably helped he was in his lap with his head turned to nose Cas’ dick through his jeans. 

Cas chuckled softly making Dean pout. The zipper of Cas’ jeans is yanked down. Soon, Dean had his cock in his mouth. 

A strangled moan escaped Cas’ mouth.

“Paying attention!” He gasped. Dean chuckled around the rapidly hardening dick in his mouth.

Dean began to lap at the underside of his cock as he slowly took it all the way in. 

The next few minutes are spent with Dean using his very talented tongue on Cas while the dark haired man sits above him withering and gasping as he tried not to buck his hips. 

“Dean! Gonna-“ Dean knew though. With a filthy pop, he dropped Cas’ cock from his mouth. A string of saliva and precome mixture was on his lips and the sight almost got Cas off right there. 

Cas sat up and laid Dean down on the couch. He had decided long ago that his favorite place to be was on top of Dean Winchester. 

He tugged Dean’s shirt over his head as Dean does the same with his. Cas looker into his eyes as he tantalizingly popped the button on Dean’s jeans and slides the zipper down. 

In one go, he pushed Dean’s pants and underwear to his ankles where the other man kicked until they are thrown somewhere else. 

Cas settled himself between Dean’s spread bow legs. Placing a thumb on the fluttering hole, he teased it just a little. 

Dean gets the picture and arched himself awkwardly to grab a bottle of lube from his end-table’s drawer. He handed it to Cas who clicked open the cap and applied it to his fingers. 

He gingerly pushed one finger in, waiting until Dean is withering and blabbering for him to move. Cas swirled the digit inside of the other man for a while until he added another. Soon he had four fingers inside of Dean and the man was a mess. 

“Cas! Cas! Please, please, plea-“ Dean’s begging was cut off by the removal of the fingers.

Wasting little time Cas kicked his jeans and underwear elsewhere before urging just the tip into Dean’s gaping hole.

His boyfriend’s pleas turn to moans and groans as Cas toyed with his nipples. 

Eventually his own need dominated his desire to tease Dean forever. He rammed the rest of the way until he bottoms out. 

The man below him let out a noise that is a cross between a scream and groan of pleasure. Cas waited only a few seconds for Dean to adjust until he was thrusting with purpose. 

A minute or two later and Dean’s strangled cry let him know he’s hit his prostate. Cas moved his angle to nail that particular spot with every thrust of his hips.

Dean was close. Cas knew he could come on his cock alone, he had done it many times before, but he decided to play nice but not too nice. Leaning over Dean he thumbed at his nipples roughly. 

Three more well placed thrusts later and Dean was painting the space between them. Cas was right behind him. 

Cas braced himself over his boyfriend on his slightly shaking forearms and smiled. 

“What were you saying about attention?” He teased and Dean huffed a laugh. 

Cas rolled off him, grabs his hand, and walks them to the bathroom to shower. 

After their shower they are both redressed and on the couch again dozing lightly.

“Love you.” Dean muttered as he burried himself further into the crook of Cas’ neck. 

“Love you too, sweetheart.” Is all he managed before he was asleep. 

———————-

Cas was smiling as he walked home. He hated leaving Dean’s, but really good sex and a post sex nap wrapped in his boyfriend had a way of making him very happy. 

Dean’s alarm had woken them both and he had to go to work on the big lead he was so excited about. Cas knew he could have laid there and waited for him to get back; unfortunately his phone notified him of a text from Michael to come home. That had been sent an hour ago. 

Cas, naturally, could not bring himself to care as he entered his apartment to his siblings annoyed glares. 

“Castiel, I would like to remind you punctuality in this business is a necessity not an option.” Hannah greeted him with. 

“Of course.” Cas rolled his eyes and lit a cigarette (clean as in he didn’t do hard core drugs, besides one could not expect him to be around his siblings without some buffer). “What’s the deal?” 

“It has come to my attention that it has been a while since our last family outing.” Michael announced. “Thus a sibling bonding errand is called for.” 

Cas barley resisted a groan and not a filthy one like he had been pulling from Dean’s mouth hours before. 

“I’ve been doing some planing,” Michael continued unaware of Cas’ extreme desires to be somewhere else. “Metatron has, as we all know, been stealing from us the last few shipments.” Cas stifled another groan at the thought of having to deal with slimy Metatron. 

“So we are all going to go to his office and remind him who the Novaks are.” Awesome. 

His siblings began to load duffles into their personal SUV. The bags clued Cas in that this wasn’t going to be pretty. Novaks rarely got their hands dirty, preferring to have others handle the bashing and bone breaking. As this is a ‘family exercise’ they would be doing the arm twisting. Literally. 

As they arrive at the office Cas prepares himself to sit in the car. 

“Castiel, come.” Anna demanded. 

“I’m get away driver. It’s my job.” Cas argueD. He really didn’t want to go in there. 

“No, that was your job.” Anna corrected. “Now that you have an actual position, you must be out in the open.” 

Cas grumbled about how it’s the middle of the night in a dark alley, it is hardly the open. His grumbling was ignored as per usual.

Part of him wanted to kick his feet and throw a fit. The other part was above that and doesn’t want to piss off his family to the point where they decide to mettle in his business. His business that has been going so well. 

So he grumbled a little more but turned the car off and followed his siblings. He kept his cigarette, however, in order to hide his nerves. 

They took the elevator and when they arrive at Metatron’s office he was already tied up and gaged. Their hands couldn’t get as dirty as necessary. 

“Metatron,” Lucifer greeted. He had always been more of a sadists then the rest of his siblings. “A little bird tells me you’ve been a bad boy.”

Cas rolled his eyes at the dramatics, but sucked his lip stud into his mouth in nervous habit, his poison stick finished in the elevator ride up. 

Michael who was in the same boat as Cas, stepped forward and threw his fist into Metatron’s nose. 

“You have lied and cheated us, Metatron.” Michael hisses. “It will not be tolerated.” 

Cas tried to make himself smaller without looking like a coward as his siblings all stared down Metatron. 

“Castiel,” Uriel’s voice snapped Cas’ attention up. “You have been extra quiet. Do you not think this man should be punished for his lack of loyalty?” 

Cas’ mouth ran dry but his face remained impassive. “Of course not. Loyalty is a foundation.” 

“Agreed,”Uriel smiled wickedly. “Why don’t you show our former friend what happens to people with such low morals.” 

Under any other circumstance Cas would have scoffed at the idea of morals and his siblings in the same sentence. Now was not any other circumstance. 

“Castiel!” Michael snapped, patience waning. 

Cas stepped forward. Took a deep breath and dislodged one of Metatron’s fingers from its knuckle. 

Metatron howled. Glancing at Michael, he received a nod to continue. Cas gulped, but before he could move again gunshots sound from outside. 

Lucifer took out his gun and placed a bullet in between Metatron’s beady eyes. 

Cas followed his siblings to the window and down the fire escape. 

His boots hit the pavement and they were running to the car just around the corner of the building. 

He heard footsteps behind them but they don’t stop. He sneaked a glance and immediately regretted it. He regretted a lot of things now. 

Right behind him with a gun drawn is the Righteous Man himself. Cas stumbled and Hannah dragged him back to his feet. 

At the car he threw himself into the driver’s seat and was met by Dean’s piercing green eyes less then fifty yards from the front of the car. Cas could practically read the heartbreak and confusion on his face. 

“Castiel!” Gadreel snapped and Cas stomped on the gas praying everyone got out of the way. 

They did. 

Cas couldn’t stop shaking the entire way home.


	6. Whoever Said All Good Things End is Getting Punched

**Summary for the Chapter:**

> Everything falls apart

“Castiel.” Hannah’s voice stopped him as he attempts to escape to his room. He needed to contact Dean, or flee the country, he hadn’t decided yet. 

“Would you like to explain why Detective Winchester seemed to know you?” 

“No.” Cas stated. He had kept Dean safe so far and he would continue, even if Dean didn’t want him anymore. 

“Would he be the reason behind your disappearings?” Hannah pressed, his other siblings stare on intently. 

“No.” Cas repeated as he turned to escape to his room. 

“Castiel, lying is unwise.” Michael called behind him. “Dean Winchester is a danger to this family and you having any contact with him is a direct betrayal.”

Cas doesn’t give him the satisfaction of answering. He slammed the door to his bedroom and locked the door. 

“Asstiel.” He heard Lucifer’s voice come through the door two minutes later. “We all saw your boy toy’s heart break, baby bro. He’s a bigger problem now then he was before, and I’m going to tear him apart piece by piece. I will make Alastair’s work look like a kiddy play date, and you’re going to watch.” 

Then he was gone, leaving Cas shaking. His worst nightmare was coming true. Dean had found out about his family. His family had found out about Dean. Now Dean was in danger. 

Cas wasn’t sure what he was doing or where he was going, but he packed a bag with cloths and his paint and slipped out the building. 

He wandered the streets and let himself drown in the city noise of dawn. 

Suddenly, a hand slammed on his shoulder and he was being shoved into the side of a building. 

“You have a lot of explaining to do.” Dean’s face was full of anger, but Cas could see the hurt festering underneath. 

“You’ve already figured it out.” Cas whispered, voice surprisingly evenly. 

“No.” Dean shoved him hard into the wall again. “Explain it to me. Like I’m the two year old you’ve been playing me like.”

“I didn’t play with you, Dean. I love you.” Cas forced himself to look into Dean’s green eyes. 

“No! Don’t say that. You don’t get to say that to me. Not anymore,” Dean’s voice broke just a little. “Was it a plan, get on the inside and destroy us? A joke? What?” 

“It wasn’t anything!” Cas screamed before forcing his voice down. “It was everything. My family didn’t know. I didn’t know who you were when we met. That’s why I ran that first day, I saw your badge and I ran. I hadn’t planned on seeing you again, but I just couldn’t leave.” 

Dean shoved himself off of Cas and he took a few steps back. He swung his fist at the brick. Cas didn’t think, much like the first time they met. He grabbed Dean’s arm to stop him from hurting himself on the building. 

Dean fell against him, desperate, holding Cas. 

“Then leave.” Dean muttered against Cas’ shoulder. 

“I can’t.” Cas gripped Dean tighter, but the other man ripped himself away. 

“Why the hell not?” His eyes were green fire, wild and blazing. 

“They’re my family.” 

“No, they aren’t. Family doesn’t start or end in blood, Cas. Have you paid attention to any part of my life?” Dean’s voice got softer. “You’re family. You’re like a brother to Sam, Jess, and Jo. You’re like a son to Bobby and Ellen. You’re like the other half of me.” 

Cas shook his head with tears in his eyes. This was so much worst then his nightmares had ever fabricated. 

“Come to the station. Make a statement. Leave an anonymous tip. We can get you off the hook.” Dean continued with tears in his own eyes. 

“I can’t.” Cas was desperate to get Dean to understand. “They’re my family.” 

“Stop saying that!” Dean was back to shouting. “They’re not your family. If a word you’ve told me about them is true, you hate them. What about your wings? Aren’t they going to carry you away? Let me be your wings.” 

“What if it was Sam?” Cas hissed. “What if Sam was hurting people. Could you turn your back on him to waste away in a cell.” 

“Sam would never, but if he did I would stop him from doing something the real him wouldn’t do.” Dean pulled his shoulders back and stared Cas down. 

“Then you and I are more different then I thought.” Cas picked up his bag from where it had fallen. 

“If you walk away right now I better not see you again, because the next time I see you, Castiel Novak, I’m going to do my job.” 

Cas hesitated for a brief second before forcing himself down the ally and further into the city. 

The sound of breaking bones echoed behind him, and he placed a hand over his mouth to stifle a sob.


	7. Choices are Simpler When Guns are Involved

**Summary for the Chapter:**

> Big stuff goes down 
> 
> My summaries suck whatever

Cas woke dizzy and confused. He had had to swim much harder then usual to reach the surface of consciousness. Now that he was awake he wished he hadn’t tried so hard. 

He was folded into a corner of an alley, which had resulted in the worst kink in his neck and a groggy soreness all over. Physical discomfort aside, he mentally felt even worse. 

A large, gaping, Dean sized hole was left in him. This was surrounded by an eternal feeling of hopelessness. The flash of betrayal and raw hurt in Dean’s eyes made him want to claw his own eyes out.

Cas debated for a significant chunk of time if he just wanted to stay there, cramped in an alley like the bag of trash he was feeling like. He would certainly have deserved it, betraying both sides of his world. Also the thought of moving only seemed to make his limbs ever heavier. 

That idea and all it’s perks was shoved aside when a nicotine craving hit him like a freight train. 

“Cigarettes.” He muttered with a mouth full of cotton. 

He shoved himself off the dirty concrete to his feet. Dizziness filled his head and he placed a hand on the building for support. If he fell he wasn’t sure he would find the strength or will to stand again. So he waited for the vertigo to pass before walking out of the labyrinth of alleyways. 

The noise hit him, a glance at his phone told him people were in full swing of their lunch breaks and that he had a full box of missed messages. He doesn’t bother himself with them, none are from Dean. 

He’s halfway to the nearest drug store when he even thinks to check for his wallet. It was a miracle it was still in his pocket having slept on the streets. At least one thing had gone right.

Before he could continued on his head was suddenly slammed against the side of a building and he was tugged around the corner. Brick dug into his back and he clenched his teeth from the increasing headache. 

“Where is he?” If Cas had thought Sam Winchester was an overgrown puppy when they first met, now he was a rabid scrape yard dog. 

“Sam-“ He was pressed further into the wall, as if Sam was trying to push him straight through it. 

“No!” He snapped dangerously. “Where is my brother?” 

“What do you mean?” Confusion was coursing in Cas, but fear was making an appearance at the desperation in Sam’s eyes. 

“Sam.” An officer Cas hadn’t noticed before with a face full of angry Winchester got Sam’s attention. 

Sam took a deep breath and backed away from Cas. The officer stepped forward, Benny who was Dean’s partner and best friend. The Cajun man was not wearing the warm smile he had at game night last weekend. 

“Castiel Novak,” Benny said. “If you would come down to the station. You’ve got some questions to answer.” 

It was phrased as a friendly suggestion but the cold eyes of the officer and Sam’s working jaw told him it wasn’t. The use of his full name told him they knew. There was no more running.

Cas nodded and allowed himself to be brought to the station. 

—————

“You’ve got a lot of nerve.” Benny, was pacing in front of a cuffed Cas. He seemed calm but Cas was willing to bet the steady pacing was nervous energy. 

“Dean Winchester didn’t go home last night.” Benny continued. “And he didn’t come in this morning.” 

Benny paused his pacing to lean over the table, six inches from where Cas was rolling his lip stud. Dean’s partner fixed a sharp look at him.

“How long did you know Dean?”

“10 months.” Cas stated, his voice sounded far steadier then the rest of him was. 

“You got really close to him didn’t you?” Benny regained his pacing. “Got real close to his family? Loved ones?” 

Cas didn’t answer. He didn’t need to. They already knew everything. They were just fishing for something else. What, Cas didn’t know. He did know he had to stay out of a cell if Dean was really in trouble. 

“Did Dean know? About your family business?” Cas picked at his finger nails. 

“When was the last time you saw Dean Winchester?” Cas stared at a really interesting part of the floor, it was like being in Michael’s office all over again. 

“Damnit, Cas!” Benny snapped, slapping his palms on the table. “I’ve got over six feet of worried Winchester out there. I’ll let him in if that’s what it takes.” 

“I don’t know where Dean is.” Cas hissed. “I saw him last night and I haven’t seen him since. If Dean is in trouble then you need to let me go.” 

At that moment Sam stormed in. If it was possible he looked even more pissed then before.

“Stop lying!” Sam charged at Cas. “He gave everything to you. He loved you! You were family!”

Benny was pulling Sam off. 

“I know, brotha,” Benny said as he grappled for a hold on the younger Winchester. “This is too much like last time, but you gotta let us work. Don’t make me put you in a cell of your own.” 

Sam stopped his struggling, chest heaving. 

“If he’s dead,” those hazel eyes bore deep into him. “I’m going to make you wish you were too.” 

“You won’t have to.” Cas returned Sam’s heavy gaze and tried to burry his guilt. 

“Do you know where he is?” Benny asked. 

“I can guess,” Cas shifted in his cuffs again. “I can show you.”

“How about just tell me?” 

“No. Take me with you.” Cas’ mind was already forming a bloody image of what was being done to Dean. “My siblings are punishing me through him. They’ll keep him alive if they can so they can shove my face in it, but if you storm in there they will shoot him.”

Both men visibly paled at the thought and Cas could feel bile rising from his stomach. He would go to jail afterwards with his family. Dean would never talk to him again. That was fine. As long as Dean had the choice not to talk to him. 

“I’ve got to run this by Chief.” Benny relented. He let go of Sam who didn’t move to follow him out. “Can I trust you in here with him?”

Sam nodded, “I just need to ask some questions. I won’t hurt him.”

“There’s eyes in here, brotha.” Benny gave Sam one last hesitant look before leaving without closing the door. 

“Was it real?” Sam asked after a long moments pause. “Any of it?”

“Yes.” Cas’ mouth tasted like sandpaper even after the offered cup of water. His nicotine headache had only increased. “I love him more than anything.” 

With the reality of Dean’s life hanging in balance, the choice that had seemed impossible last night was impossibly simple now. Dean was right, the betrayal in Sam and Benny’s eyes was proof of that, this was his family. 

“Okay.” Sam bursted into action. He walked bristly over to Cas, knelt down, and pulled something out of his pocket. 

Cas stared in wonder as his cuffs clicked open. Shock was overflowing his system, but Sam was already moving again. 

“What?” Cas couldn’t form an actual question as he stood and rubbed his wrists. 

“It’s going to take them too long to get all the legal paperwork. Dean isn’t even in the city is he?” Cas shook his head and Sam turned his attention back to the barred window. “Last time-.”

Sam’s shoulders threatened to shake and he struggled to fit his screw driver into the screw. Cas stepped forward and gently took over the task. 

“What about the camera?” He gestured to the device in the ceiling Benny has warned Sam about. 

“Charlie, a tech girl here, has got it covered.” Sam explained as he helped Cas set the bars quietly on the table. 

Looking out the window, there was a fire escape about four feet from the little window. Cas had serious doubts he was going to fit through there, let alone Sam’s tall frame. Glancing down he saw they were at least five stories up. 

Before he could voice these concerns, Sam pretzeled his body to fit through the window, then like a fucking mountain goat, jumped to the ladder. Cas poked his head out after him and stared in disbelief. 

“Come on.” Sam ordered, clearly still not friendly with Cas, and began to climb down. 

“I could really use a cigarette.” Cas grumbled, but followed Sam all the same, if a little less graceful.

Cas’ feet smarted against them pavement seconds after Sam’s. The other man paid him no mind as he briskly walked into the parking lot and to Sam’s Chevrolet Charger Dean always made fun of him for. The thought caused a lump to rise in his throat that he had to force down. 

Cas gave directions to Sam as they drove, but there wasn’t nearly enough turns to point out to occupy his mind. Sam wasn’t offering conversation. He sat full of a adrenaline filled energy paired with fury and worry. 

Dean wasn’t dead. Part of him knew that. The other part was filled with other -if maybe a little far fetched- circumstances. Images of Lucifer cutting Dean open and laughing made him literally shake his head in an attempt to forcefully remove the thoughts from his mind. The movement did nothing to rid his imagination of the gory thoughts, if anything Sam’s knuckles clenched impossibly tighter around the steering wheel. 

As they drove Cas wasn’t sure which to expect. Sam himself seemed torn. The lawyer was either going to burst at any second or he was going to keep his fiery tense silence. 

Cas didn’t plan on rubbing him either way. He instead mapped out the exact route to the warehouse his siblings used for their more unsavory practices. Cas himself had never been there, but he knew of it. His siblings knew he knew as well, they were counting on it. 

Taking one last left they pulled into the parking lot and Sam cut the engine. He pulled a gun from his waist band and checked the clip with practiced hands. 

He handed another to Cas that he pulled from the glove box. Before leaving the car he gave Cas a stony look. 

“When this is over,” Sam said dangerously. “I’m going to make sure you all go away for a very long time.”

“Sam,” Cas needed to say something. He had to put to words to explain the rotting feeling inside. “You can put me away for a thousand years, but I will never forgive myself for putting Dean in harms way.” 

“Good.” Was Sam’s clipped answer as he unfolded himself from the car. Cas followed. 

“I’ll go first.” Cas’ voice sounded far away to his own ears. He wasn’t ready to see behind the door. A glance at Sam told him neither of them were. 

The door was unsurprisingly unlocked. It swung open slightly and they both slipped in. Leaving the door open behind them. 

The warehouse wasn’t dark, as he had stereotypically assumed. From there however, it was everything he and horror movies had ever pictured. It was hard dirty cement walls and floor. The walls had neatly arranged racks of various tools precisely cleaned and polished. 

All the little details were shoved from his mind as his eyes focused on a table in the middle space. More specifically they focused on the man chained to it. Even from the distance Cas could see the blood, both fresh and drying. 

Next to him Sam was already charging forward, like a bull. Cas placed his arm across Sam’s chest to prevent him from moving. 

“Cas,” Sam hissed, obviously trying not to shoot him on the spot. 

Before Sam could threaten him Michael stepped towards the table. Cas could see his brother’s eyes were trained on them. 

“Castiel.” He called, voice echoing throughout the space. “I’m glade you came, and I see you brought Samuel Winchester as well. I do love matching sets.” 

Cas didn’t move. Didn’t speak. Any sort of plan be had been able to muddle together in the car was gone from his mind at the sight of all that blood. Dean’s blood. And his brother standing over his boyfriend. 

From what he could tell Dean was unconscious, but seemed to be stirring at the voices. There was too much blood wasn’t there? How much was too much? 

“Lucifer did a nice job on your toy,” Michael’s voice snapped him out of his thoughts. “I don’t think he’s had so much fun in a long time.” 

Cas heard Sam actually growl, a sound he had heard Dean make only once before, when a guy had been too handsy with Cas at a bar. Fleetingly he wondered if the Winchesters were part animal. Wolf or another type of dangerous predator. He certainly felt like prey at the moment. 

“Step away from my brother.” Sam had found his voice and had raised his gun to be aimed at Michael’s chest. 

“Ah, Sam.” Michael placed a hand in Dean’s cheek and Cas thought he might vomit at the sight. “As glade as I am to see you. This is for my little brother. We’ll get to you in a moment.”

“Michael,” Cas’ voice sounded stronger to his own ears them he felt. “This is for my betrayal. Punish me. Dean Winchester has nothing to do with this. He didn’t know who I was.” 

“Now you know that isn’t true, brother. Yes you betrayed us, but you did it for him. Therefore you find him more important then your family, and that simply won’t do.” 

Dean took the time to wake. A pained sound left his mouth. Cas heard it once and decided he never wanted to hear it again. Dean’s head turned to face them, the blood on his face catching the light.

“Cas? Sammy?” Confusion painted his still beautiful face. “Cas, I’m sorry but I think family dinner might be a little awkward.” 

Cas was caught somewhere between a humorless chuckle and a scream. Even tied to a table, tortured, Dean fucking Winchester had to crack a joke. It made Cas’ chest hurt that much more. 

“Dean Winchester, your reputation procedes you.” Michael sneered. 

“Glade I’m living up to your fangirl fantasies.” Dean’s broken lip split further with his teasing smirk. 

“As I was telling my dear little brother, you are going to be the subject for a little educational lesson.” Michael trailed a finger through a cut on Dean’s cheek. Dean stifled a grunt in pain, another noise Cas adds to his list of least favorite noises. 

“Like hell.” Sam snapped. Cas raised his gun and the flick of the safety seemed to crack through the building. 

Apparently the sound wasn’t his imagination because Michael drew his own gun and rested it in the middle of Dean’s forehead. 

“Who do you think will be the quicker draw, Castiel? Come on, you worked with numbers. Do the math and tell me which bullet will hit it’s target first.” Cas could hear the blood rushing in his ears. Helplessness was choking him. “Lucifer just stepped out for some more rock salt. I suspect he will be back shortly. Then we may continue.”

There was nothing he could do. Cas had never felt so helpless in his entire life. Even Sam, one of the sharpest minds in the city seemed to be at a lost. 

“So what?” Dean spat, a fire ever blazing inside him. “We’re just going to sit here and braid eachother’s hair?” 

“Dean, I do love your spirit.” Michael tapped Dean’s cheek. “It makes me wish we hadn’t let Alastair have you the first time.” 

Dean and Sam both visibly flinched at the mention of the memory. Cas briefly considered puking in the corner. He had long tugged his lip stud into his mouth. Suddenly an idea came to mind. 

“Michael, I’ve learned my lesson.” Well, it was more of a last ditch, desperate, half formed concept. “Let Dean and Sam go, and I’ll never see them again. I’ll go back to my position at the business, even take out my piercings and wear nothing but suits. I’ll marry the son of a rich business man you pick out. You’ll never hear me complain.” 

“Cas-“ Dean tried to cut in and was wrestling with his binds. Cas forced himself not to look at him and continue. 

“You could even put a bullet in me.”

“No!” Dean roared and thrashed. 

“As tempting as all that is.” Michael seemed only amused at Cas’ offer. “Killing this man will hurt you so much more than losing your freedom ever would.” 

“Killing me will get less police and media attention.” Cas scrambled. “Dean is important to them. We won’t be able to stay here. We would have to flee, destroy Novak Industries.”

“Castiel-“ Michael has that patronizing glint in his eyes Cas had hated since he was a boy. He wasn’t going to stand for it anymore. Dean was his wings, and he was going to carry him away. 

“Then I’ll do it myself, fuck your lesson.” Cas lined the gun barrel up underneath his chin. 

“Cas!” Dean thrashed harder and he had a desperate look in his eyes. 

“Cas.” Sam next to him hissed and reached for the gun. 

“Sam, you touch me and I’ll blow a hole in my head.” Cas’ voice was way too calm for this. He deserved a damn acting award for appearing so fucking chill. 

“Castiel, don’t be ridiculous.” To anyone else Michael might have seemed unaffected, but Cas had grown up watching that chain of armor, he knew when there was a kink in it. The tiniest flash in his oldest brother’s gaze told him a lot. Michael wanted Cas to learn a lesson, he didn’t actually want to physically hurt his brother. What he didn’t understand was that loosing Dean would be worse. 

“Let them go, don’t hunt them down. Or I’ll shoot.” Cas’ gaze stabbed into Michael’s. “Who do you think will be the quicker draw, brother?” 

The silence was thick in the building. Cas’ breathing sounded like crashing ocean waves in his own ears. Michael seemed to be contemplating something, either if Cas was serious or if he could shoot Dean quicker then Cas could shoot himself. 

Bang. 

A shot rang out. Cas flinched and just about pulled the trigger on his own gun. Michael’s weapon was thrown across the room. Sam, next to Cas pulled his finger off the trigger. 

Cas took the destruction and stalked towards his brother. Michael had always been taller then him, both literally and metaphorically, now he finally felt all six feet of himself. 

“It’s over.” Cas said, gun to his brother’s chest. “All of it.” 

“Brother-“ whatever Michael had to say was interrupted, and it wasn’t Lucifer with the rock salt. 

“Drop your weapons!” Chicago police stormed the building, all dressed in swat gear. 

Cas flicked the safety back on and dropped his gun, eyes never leaving his brother. He ached to be with Dean. He was less then three feet from him, but it didn’t matter. 

Handcuffs were secured around his wrists for the second time in that very long twenty-four hours. 

Dean called for him as he was unchained and removed from the building on a medical gurney. Cas forced himself not to run to him. He hadn’t lied. It was over. All of it. 

—————-

He was being detained while they waited for the trial. He had heard Dean was going to make a full recovery. It had eased his heart just a little. 

It had been three weeks now. Cas avoided his siblings. Went about his caged days in a numb state. He read and ran laps around the yard. His fingers itched to paint, but he settled for sketching images on a notepad with a pencil he had been granted. The drawings suitably all in tones of gray. 

He was back to the prison bars theme he had been in nearly a year earlier, before he had felt what it was like beyond those bars. Now he had a front row seat with them and he didn’t have to imagine the details. 

When a guard came and got him telling him he had a visitor, Cas asumed it was the state lawyer he had been given, Naomi, who appeared to always be sucking on the worlds sourest lemon. So he sighed and followed the guard to the visiting area. 

Plexiglass separated the inside from the out. Cas idly decided it might be the focus of his next piece. The man who caught his attention blew any and all thought from his head. 

He sat and stared. Not for the first time he wished the prison hadn’t taken all his piercings, but he settled for capturing the corner of his bottom lip between his teeth instead. 

“Cas?” Dean looked good for the most part. Stitches were holding together his top lip and he had impressive bruising, otherwise he looked relatively unharmed. If a little tired with dark bags under his eyes. 

“Dean, I-“ Words got stuck in his throat and he wanted to cry. 

“I know.” Dean winced as he tried to smile, Cas mirrored the movement as if the pain was his own. “It’s not your fault, Cas.” 

“What part of this isn’t my fault?” 

“They wanted me off the playing table even without you, right?” Cas didn’t know what this was, but he wished Dean had stayed away. 

“No. I knew from the beginning I was putting you in danger. I should have never seen you again after that first night.” Dean looked devastated at Cas’ words but he pushed on. “Please go. Nothing you can say will make me feel better or worse about myself.” 

Cas moved to go. This lock up thing would be so much easier if he stayed in his numb state and accepted his fate. 

“Cas, wait!” Dean called behind him. The strength Cas had had to ignore him in the warehouse was gone, due to pure curiosity or just plain weakness he did my know. “Sam agreed to take your case.” 

That got Cas’ attention. He sat back down. 

“What? Why?” 

“I don’t blame you.” Dean’s gaze was almost too intense. “You were there to save me. You worked in numbers right? That isn’t technically illegal. Sam thinks he can spin this to get you off the hook.” 

“Why would he want to?” Cas hadn’t seen Sam since the warehouse, but he couldn’t imagine his feelings towards Cas had changed so drastically. 

“ ‘Cause I told him to.” Dean gives a careful smile this time. “Kid’s still my little brother.” 

“I don’t get it.” Cas’ brain wasn’t connected, he was still convinced he had left it way back on the road to get ran over by that car way back when. 

“I love you.” Dean stated as if that explained everything. “That hasn’t changed. You haven’t changed. I don’t believe that our entire relationship was a lie.” 

“Dean, I’m in lock up. What if Sam doesn’t get me out? I’m facing a lot of years.” Cas bit back saying he loved Dean too. 

“So? Then I’ll be one of those prison wives or whatever, you know, like the reality tv shot were their husbands are in lock up?” Dean had humor in his eyes. 

“You watch too much tv.” Cas couldn’t help but say. 

“Besides, orange isn’t your color.” 

“I love you too.” Cas couldn’t hold on anymore. 

“Time’s up.” The guard said and walked up to Cas. 

“I’ll see you soon.” Dean’s loving gaze is the last thing he saw before the heavy metal door closed again. It felt a little thinner now.


	8. Things are Happy because Life Can Sometimes be a Fairytale

**Summary for the Chapter:**

> Things are happy again 
> 
> One more before the epilogue (this was supposed to be it but I couldn’t do it so yeah or nay)

Cas was buzzing. His fingers itched and he could hardly cease his bouncing knee. It had been two months. Two damn months in the prison with bleak walls, bleak floors, and even bleaker faces. 

Dean came to see him each of his fourteen allowed times. He brought a light to the facility and it made Cas’ heart ache evermore to be behind the plexiglass. During those precious minutes, after they had gotten some things off their chest the first time, they settled back into their normal conversations with teasing and laughter. It was his only thing to look forward to. 

Now he was going to see him without the glass, cuffs, or ugly prison uniform. His knee started to bounce again. The corner of his bottom lip caught his lip piercing, thankful to have them back with only his eyebrow hole closed up. 

The only reason Cas was granted the ability to feel like this was Sam. The semi-famous lawyer had bumped Cas’ case up and gotten him out, Sam had gotten him cleared of all charges. He pulled up points of Cas being mostly unaware of his sibling’s more sinister plans and not going to the police out of fear. 

Honestly, Cas hadn’t felt to right playing overly innocent victim, but one look at Dean and he had to be free. His guilt was completely pushed aside when the other lawyer had tried to insinuate that Michael not shooting Cas hinted at them working together for Dean’s kidnapping and torture. The fucking nerve, Cas could have sworn a vein might burst out of his head. Sam had shot that down so fast, the jury didn’t even get a chance to let the new point of view settle. 

None of that mattered now. He was waiting in the slightly less bleak parking lot, waiting for Dean and Baby. His sketch pad from prison was on his lap and he was sketching Dean’s face from memory with the color pencils Dean had managed to get for him. 

A loud roar sounded through the lot, causing Cas’ head to snap up. Dean’s impala was a sight for sour eyes, the man behind the wheel was an even better sight. Even though they had decided for Dean to pick him up from the prison at three, an evil part of him still held to the possibility Dean wouldn’t show. 

That thought had been put through the shredder and burned. Dean was wearing a similar dopey smile to Cas’. He looked brighter out here if that was possible. He looked like home. 

Cas couldn’t contain himself long enough for Dean to scramble out of the car. He ran over to where the impala was crookedly parked. Opening the driver’s side he tackled Dean down into a hug. 

Cas’ duffle was dropped somewhere outside the car, his sketchbook and pencils scattered. None of that matter because Dean was kissing him. His lip and bruises completely healed. He had almost forgotten how perfectly Dean’s lips fitted with his own, or how much Dean liked to tongue at the piercing on his lip. 

He was tugging at Cas’ jeans before Cas turned his brain back on. 

“Maybe we should get out of the parking lot before we get put back in the place I just left for public indecency.” Cas managed. 

Dean pouted, huffed, sighed, and grumbled in that order before helping Cas pick up his few belongings and placing them in the backseat. As they pulled out of the parking lot, Cas stuck his middle finger out the open window at the building. Dean laughed and did the same. 

Dean stopped laughing when Cas took his hand and placed it firmly over Dean’s crotch. A desperate, barely stifled whimper came from the other man as Cas palmed the growing hard on. 

They barely made it around the corner and out of sight of the building when Dean pulled on to the side of the road, a secluded road thankfully, and they were on each other all over again. Cas shuffled Dean around so he was laid out across the bench seat. He straddled the man’s hips and admired him for a few gasping breaths before Dean started to grow restless. 

“Draw later, fuck now.” Dean bucked his hips into Cas’ growing erection. 

Later he would do this right, taking his time. He would carefully pull Dean apart under him before piecing him back together. Now he pulled Dean’s jeans and boxers down and grabbed the lube they kept in the car for just such occasions and pressed a finger into Dean. 

“Oh.” Cas was surprised to find Dean already prepped. “Someone is very eager.” 

“And someone is very impatient.” Dean grumbled, but fucked himself on Cas’ single finger while Cas took out and lubed his dick. 

Anything witty that he could have said was lost as he carefully pressed in. Oh fuck. Dean was as perfect as ever. 

“Still so tight.” Cas groaned and Dean groaned underneath. 

“I’ll bet, it’s been a month.” Dean shuffled, signally Cas to continue and bottom out. 

“I could fuck you three times a day for the rest of our lives and this hole would still be as tight as the first time.” 

“Wanna test that?” Cas didn’t responde to Dean, but instead pulled his hips back before thrusting back in roughly. 

Dean moaned underneath him, his hands gripping Cas’ shoulders. The angle was a little awkward but it wasn’t anything they weren’t used to. Cas got a steady rhythm going, finding Dean’s prostate on the third thrust. 

Through Dean’s Metallica shirt, he rolled his nipples, causing whimpers and gasps to escape the other man. Fuck, he had missed this. Dean was perfect through and through. 

“Cas! Gonna come.” Dean blabbered. 

Cas pulled him in for a filthy kiss, more teeth then anything. “Come for me, sweetheart.” 

Dean came in long spurts. Cas carefully made sure none of it touch the leather. Instead allowed it to paint both their shirts, the sight pushed him over the edge with a moan and he came deep inside Dean. 

He carefully pulled out and wedged himself next to Dean. Heavy panting filled the car. Normally he could fall asleep, that was the first time be had came since he had been arrested -the ratio of privacy to pervs too skewed for his liking-, but excitement was still buzzing. He wanted to see his family again. 

A realization struck him and a little bubble of laughter escaped his lips. Suddenly the laughter grew to a point borderline hysterical. Dean looked at him confused, before catching his contagious glee. 

“Why are we laughing?” Dean asked between giggles and snorting. 

“Because I wasn’t even out five minutes and we already had sex and we have cum on our shirts.” Cas managed to explain. 

Dean looked down at his temporarily ruined shirt and laughed harder. That’s how they spent the next fifteen minutes, sometimes it would start to dwindle then one of them would start again and the other would join. Cas was high as a fucking kite on hysteria and dopamine. 

“I love you.” Cas said as they finally started to come back to earth. 

“I know.” Dean rolled into him and began kissing at his neck. 

“Star Wars, right?” Cas asked, tilting his neck to give him more access. Dean just hummed and began working on leaving an impressive hickey on Cas’ collarbone. 

“Aren’t they waiting for us?” Cas didn’t bother moving to check the time on his phone. 

“I told them I was picking you up at four.” Dean shot him a cheeky grin. They had planned on Dean’s arrival at three. 

“I love you.” Cas captured Dean’s lips with his own. 

“I love you, too.” Those were the last words said for a significant amount of time. 

Trading kisses in the back seat like teenagers, covered in their own and each other’s cum, there was no place Cas would rather be. He could never capture the deep emotions in the front seat of that car in a thousand paintings. Instead he traced Dean’s body with his fingers and lips. 

“We should go.” Dean finally pulled away. “We need new shirts and I need to get cum out of my ass thanks to someone.” 

“You loved it.” Cas allowed Dean to get back in the driver’s seat. 

“Dick.” Dean huffed with a smile. 

They both fixed their pants they had left pulled down and buckled their seatbelts before taking off down the road again. Cas absorbed all the colors of the countryside -mostly greens, yellows, and blues- before it turned to cityscape. For the first time this city felt truly like home. 

They change at Dean’s apartment, Cas had a single change of cloths in his duffle. A quickie was squeezed in where it probably shouldn’t have since they were already late. Sue them though, they hadn’t been able to touch each other in two months. 

It’s 5:15 when they pull up to the Roadhouse, Ellen had closed it for just this occasion. 

“Are we going to be in trouble?” Cas asked as they leave the car. 

“Nah, they’ll give us some crap but they get it.” Dean gave him a deep look. “You know they don’t blame you, right? It’s all in the past.”

“I would understand if they didn’t.” Dean laced their hands together. 

“If Sammy forgives you, the rest of them do, and if not, I’ll have a talk with them.” Cas took comfort in Dean’s words. 

They walk hand in hand into the Roadhouse. Inside was Bobby, Ellen, Jo, Sam, Jessica, and new baby Maddison (Maddie) Deanna Winchester. A banner over the bar read Welcome Home Cas and it almost made him cry. 

He even held his emotions through the hugs he got from Sam, Jess, Ellen, jo, and even Bobby.

“Good to have ya out of the slammer, son.” Bobby’s gruff statement was what brought open the flood gates. Dean kept an arm around his waist, keeping him close and kissing at his tears. 

They ate buffet style with Cas’ favorite burgers and a peanut butter jelly cake Jess had made. Dean did a little grumbling about it not being pie but still stole some from Cas’ plate. 

Now he was watching Dean play with two month old Maddie from across the room.

“He’s so good with her.” Sam came up to him, his second beer in hand, and gestured to his older brother with his daughter. 

“Yeah, he wants some.” It felt surreal to say out loud. Cas had never thought about having kids himself, now it sounded like the best idea in the world. 

“He practically raised me, he is going to be a great dad.” Sam looked at Cas. “You are too.”

With that emotional bombshell dropped, Sam walked over to Jess at the bar. She had gladly handed over little Maddie to her uncle to get a couple minutes to herself. 

He wasn’t on the sidelines anymore. There was nothing stopping him from going over there. So Cas set down his beer and walked over to Dean and Maddie. 

“You want to hold her?” Dean asked as Cas approached. 

“Oh, umm. I don’t-“ Dean didn’t let Cas finish, he plopped the baby in Cas’ tattooed arms without any warning. “Dean!” 

“It’s okay.” Dean soothed Cas, not Maddie who looked up at him with amusement in her new born blue eyes. “You’re gonna scare her if you freak out. Support her head, there you go. See, she’s more durable then she looks. Tough like her uncle Dean, aren’t you, sweetie.” 

Cas’ heart melted just a little at Dean’s cooing. He looked down at the little bundle and couldn’t stop his smile. One day. For now he was going to spoil her rotten along with her uncle. 

Cas looked up to the bar filled with his family he had found. Well, they had really found him. Well, not even that, they had come attached to this amazing man he had pushed out of the way of a car. 

The future was uncertain, he didn’t have a job yet -he would be staying with Dean who wasn’t concerned “we’ll shower together so the water bill doesn’t go up”-, his siblings didn’t get life sentences so that could potentially be awkward. What he did know was wherever his wings took him, the Righteous Man of fucking Chicago and his family would be with him the whole way.


	9. Epilogue: Marathons are for Fuckwads (Now I Sound Like My Husband)

**Summary for the Chapter:**

> Yeah! Fluffy epilogue

Three Years Later...

Cas’ breathing came in pants, his skin was sticking and he was deeply regretting some certain life choices. This had been his worst one by far. Who in there right mind had twisted his arm and made him consent to this fucking thing. Now he was starting to sound like Dean. 

“Cas!” There his husband was now, holding a water bottle in one hand and balancing two and a half year old Claire with the other another on his hip. Her younger brother, Jack, was in his carrier contained and sleeping being almost a year old and just to begin to walk. 

They had only planned on one to start. However, with a mother who died birthing Jack and a wayward father, neither could live with the thought of splitting the two siblings apart. So they had become a family of four, taking home fourteen month Claire Mary and three month old Jack Samuel, and Cas loved them all so damn much. 

Now he had to physically forced himself walk over to his family. 

“That was dumb,” Cas said, taking the water. “Don’t ever let me do that again.” 

“Come on, Cas it wasn’t as bad as the last one.” Sam had a stupid smile on his face Cas didn’t appreciate. He placed a kiss on Jess’ cheek and one on bored, three year old Maddie’s. 

“Never again.” Cas vowed. He dropped his head to Dean’s shoulder. 

“Papa is gross!” Claire exclaimed, swinging a hand at Cas’ sweaty head. 

“We don’t hit, Claire.” Dean gently grabbed their little girl’s arm. “Yes Papa does smell, doesn’t he.” 

“Pew yew! Daddy does to!” Maddie said, plugging her nose. 

“Oh really?” Sam scooped up his daughter, all sweaty. Maddie squealed and giggled until Sam rested her on his hip. 

“I’m going home and sleeping until I’m fifty.” Cas said, grabbing Jack and his things before following the others to the parking lot. 

“Don’t you have a deadline?” Dean asked, clearly amused. 

“Naomi can shove her deadline up her left nostril.” Cas had needed to learned to censor his language, especially with Claire repeating every word they said at daycare. 

“He’ll be up by elven tonight finishing it up.” Dean told Sam and Jess with a knowing grin. 

“It’s practically finished anyway. I could send it in now.” Even though he didn’t mean it. They all knew Cas wasn’t going to leave his piece without finishing touches. 

He was employed by a charity company that sold paintings to museums, stupid rich people, and other parties. A high percentage of the funds went back to a whichever cause they had voted for that year. The money always found its way back to the people of Chicago, fixing infrastructure, updating schools, and others. 

This year’s charity was helping youth involved in domestic violence. Everything about it shattered Cas’ heart, now more then ever with kids of his own. He had been working on the piece for the better part of six months. 

“Well, see you guys Friday.” Jess said. Friday was trivia night at the Roadhouse. She gave Dean a hug, a kiss to Claire and Jack, and a last minute wave to Cas after remembering what Claire had said. 

“We’re gonna wipe the floor with you!” Dean called as his brother, sister-in-law, and niece walked towards their car. 

“You wish, jerk.” Sam volleyed back. 

“Bitch!” Cas covered his daughter’s ears in time for Dean’s response. “That’s not a bad word, Cas.” 

“Do you want another phone call saying Claire was calling the others that?” Cas raised his eyebrow while strapping his son into the back seat of the impala. 

“That was a formality, Billie loves me.” Cas rolls his eyes at his husband who was buckling Claire into her flowery car seat. 

They drove the fifteen minutes to the outskirts of the city where the tall buildings turned into rolling fields. Cas had been hesitant to move out to the countryside for their family home. He had grown up in the city and maybe it hadn’t been perfect but he couldn’t imagine growing up any where else. 

Then they saw the house. A four bedroom, two bath, older white farm house. It sat on three acres of woods, a field of wildflowers, and a small creek. He had thought it was too picturesque, like something out of a magazine that wasn’t really a home, but he had seen Dean’s face. He had heard Dean’s excited blabber about the extra bedroom being perfect for Cas’ work space. 

His new husband had fallen in love with the property. It was private and he wouldn’t worry about their future kids running around to their heart’s content. Cas could see how it was everything Dean had ever wanted to give his family, so he had given it a shot. 

It had needed a little work, work their family was more then happy to help with. They pulled up the butt ugly carpet that covered it throughout, replacing it with hardwood and soft new carpet in the bedrooms and living areas along with new furniture they had scrapped together. Other then that it had only needed a fresh coat of paint that Cas took upon himself. 

Dean had given him complete trust over the colors and designs. With his trust he had decided to go as bold as he wanted. The living room was a deep orange, a large blue W for their last name Winchester was in the center now being surrounded by framed photos. The dining room was painted a simple soft grey with flowers on the ceiling in a hundred different reds, oranges, and yellows contrasted with deep blue ones scattered throughout. 

The kitchen he had done in navy to correlate with the attached dining room, white cabinets and light counter tops kept it bright. Both bathrooms he did in a lighter dusty orange in comparison to the blaze in the living room, accented with a black and grey city scape in the main floor bathroom and turquoise fish and whales in the upstairs one. 

His and Dean’s room was the only place in the house he used green. It was a dark emerald that reminded him of his husband’s eyes. On an accent wall Cas had broken out his spray paints and created a grey scale mural with a silhouette of a winged man and non winged man walking hand in hand above a city scape. Cas’ signature electric blue streak cut through it. Dean had blushed hard when Cas had shown him, then promptly tackled his paint splattered husband onto their plastic covered bed. 

When Jack and Claire came along he allowed Dean’s help. Together they painted stripes of neutral blues, research said it was soothing, with a large tree and red apples spelling out Jack. For their daughter they did periwinkle with shiny stars and bluebirds and cardinals, swirling calligraphy scrawled out her name. 

Now as they walked in through the sky blue door, Claire running to the living room scattered with toys, her brother free from his carrier following clumsily at her heals, and his husband moving to the kitchen to start lunch, it was more of a home then Cas had ever known. Following Dean to the kitchen, he couldn’t help steal a kiss or two. 

When the quick kiss began long, drawn out, and passionate Dean pulled away and gave him a smile. 

“What’s that for?” He asked.

“Nothing.” Cas had a dopey smile on his face, maybe he had more of a runner’s high then he had thought. “I‘m just really glade I let my brain get squashed by that car.” 

Dean gave him a confused look. “I love you too?” Cas just kissed him again. 

“Eww!” Claire screeched from the living room. 

“Eww!” Jack copied his big sister. 

“Eww!” Dean said, causing their kids to giggle. 

Cas laughed with them and was shooed out of the kitchen to shower. 

He climbed to stairs to the orange bathroom. As he peeled off his layers he caught sight of a single green eye with DW JW CW in the iris over his heart covering a light blue rose that use to sit there. It was his newest ink and his favorite. 

As he turned to turn on the water his back caught his eyes next. His wings inked proudly into his skin. They still spread across his back down to his broken bone tattoos at his wrists. He smiled fondly at the feathers. They had served him well, but he didn’t need them anymore.


End file.
